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Publications Tropomyosin Receptor Kinases (Trk)

Bernard-Gauthier, V*.; Mossine, A.V.; Mahringer, A.; Aliaga, A., Bailey, J. J.*; Shao, X.; Stauff, J.; Arteaga, J.; Sherman, P.; Grand'Maison, M.; Rochon, P. L.; Waengler, B.; Waengler, C.; Bartenstein, P.; Kostikov, A.; Kaplan, D. R.; Fricker, G.; Rosa-Neto, P.; Scott, P. J. H.; Schirrmacher, R. (2018). Identification of [18F]TRACK, a fluorine-18-labeled tropomyosin receptor kinase (Trk) inhibitor for PET imaging. Journal Medicinal Chemistry (cover image February). 61(4): 1737-1743.

Mossine, A.V., Brooks, A.F., Bernard-Gauthier, V.,*, Bailey, J.J.,* Ichiishi, N., Schirrmacher, R., Sanford, M.S., Scott, P.J.H. (2018). Automated synthesis of PET radiotracers by copper-mediated 18F-fluorination of organoborons: Importance of the order of addition and competing protodeborylation. J Label Compd Radiopharm. 61(3): 228-236.

Bailey, J.*, Schirrmacher, R., Farrell, C*., Bernard-Gauthier, V*. (2017). Tropomyosin receptor kinase inhibitors: an updated patent review for 2010-2016 – Part II. Expert Opinion On Therapeutic Patents. 27(7): 831-849.

Bernard-Gauthier, V*, Bailey, J.J., Mossine, A.V., Lindner, S.K., Vomacka, L., Aliaga, A., Shao, X., Quesada, C.A., Sherman, P.S., Mahringer, A., Kostikov, A., Grand'Maison, M., Rosa-Neto, P., Soucy, J.-P., Thiel, A., Kaplan, D. R., Fricker, G., Wängler, B., Bartenstein, P., Schirrmacher, R. and Peter J. H. Scott. (2017). A Kinome-Wide Selective Radiolabeled TrkB/C Inhibitor for in Vitro and in Vivo Neuroimaging: Synthesis, Preclinical Evaluation and First-in-Human. Journal of Medicinal Chemistry (Scott and Schirrmacher share last authorship) (cover image August). 60(16): 6897-6910.

Bailey, J.*, Schirrmacher, R., Ferrell, K.*, Bernard-Gauthier, V.*. (2017). Tropomyosin receptor kinase inhibitors: an updated patent review for 2010-2016 – Part I. Expert Opinion On Therapeutic Patents. 27(6): 733-751.

Bernard-Gauthier, V.*, Vesnaver, M.*, Mahringer, A., Fricker, G., Schirrmacher, R. (2017). Design and synthesis of a fluorinated quinazoline-based typeII Trk inhibitor as a scaffold for PET radiotracer development. Bioorg Med Chem Lett. 27(12): 2771-2775.

Bernard-Gauthier, V.*, Schirrmacher, R. (2015). Evaluation of WO2015042088 A1 - a novel urea-based scaffold for TrkA inhibition. Expert Opinion on Therapeutic Patents. 26(2): 291-5.

Bernard-Gauthier, V.*, Bailey, J.J.*, Berke, S.*, Schirrmacher, R. (2015). Recent Advances in the Development and Application of Radiolabeled Kinase Inhibitors for PET Imaging. Molecules. 9(20): 22000-27.

Bernard-Gauthier, V.*, Bailey, J.J.*, Aliaga, A., Kostikov, A., Rosa-Neto, P., Wuest, M., Brodeur, G.M., Wuest, F., Schirrmacher, R. (2015). Development and first in vitro evaluation of fluorinated (2-pyrrolidin-1- yl)imidazo[1,2-b]pyridazine pan inhibitors as candidate PET imaging radioligands. MedChemComm (HOT article). 6: 2184-93.

Bernard-Gauthier, V.*, Aliaga, A., Aliaga, A., Boujemeline, M.*, Hopewell, R., Kostikov, A., Rosa-Neto, P., Thiel, A., Schirrmacher, R. (2015). Syntheses and evaluation of carbon-11 and fluorine-18 radiolabeled pan-tropomyosin receptor kinase (Trk) inhibitors: exploration of the 4-aza-2-oxindole scaffold as trk PET imaging agents. ACS Chem. Neuroscience. 6(2): 260-276.

Bernard-Gauthier, V.*, Schirrmacher, R. (2014). 5-(4-((4-[18F]fluorobenzyl)oxy)-3- methoxybenzyl)pyrimidine-2,4-diamine: A selective dual inhibitor for potential PET imaging of Trk/CSF-1R. Bioorg. Med. Chem. Lett. 15: 4784-4790.

Publications SiFA

Justin J Bailey, Melinda Wuest, Michael Wagner, Atul Bhardwaj, Carmen Wängler, Bjoern Wängler, John F Valliant, Ralf Schirrmacher, Frank Wuest. Synthesis and Preclinical Evaluation of [18F]SiFA-PSMA Inhibitors in a Prostate Cancer Model. J. Med. Chem. 2021,64,15671−15689.

Beyer, L., Gosewisch, A., Lindner, S. et al. Dosimetry and optimal scan time of [18F]SiTATE-PET/CT in patients with neuroendocrine tumours. Eur J Nucl Med Mol Imaging 48, 3571–3581 (2021).

Unterrainer, Marcus; Lindner, Simon; Beyer, Leonie; Gildehaus, Franz J.; Todica, Andrei; Mittlmeier, Lena M.; Jurkschat, Klaus; Wängler, Carmen; Wängler, Bjoern; Schirrmacher, Ralf; Tonn, Jörg C.; Albert, Nathalie L.; Bartenstein, Peter; Ilhan, Harun. PET Imaging of Meningioma Using the Novel SSTR-Targeting Peptide 18F-SiTATE. Clinical Nuclear Medicine 46(8):667-668.

Gower-Fry, L., Kronemann, T., Dorian, A., Pu, Y., Jaworski, C., Wängler, C., Bartenstein, P., Beyer, L., Lindner, S., Jurkschat, K., Wängler, B., Bailey, J. J., & Schirrmacher, R. (2021). Recent Advances in the Clinical Translation of Silicon Fluoride Acceptor (SiFA) 18F-Radiopharmaceuticals. Pharmaceuticals, 14(7), 701.

Cheng, X., Hübner, R., von Kiedrowski, V., Fricker, G., Schirrmacher, R., Wängler, C., & Wängler, B. (2021). Design, Synthesis, In Vitro and In Vivo Evaluation of Heterobivalent SiFAlin-Modified Peptidic Radioligands Targeting Both Integrin αvβ3 and the MC1 Receptor—Suitable for the Specific Visualization of Melanomas? Pharmaceuticals, 14(6), 547.

Wurzer, A., Di Carlo, D., Herz, M. et al. Automated synthesis of [18F]Ga-rhPSMA-7/ -7.3: results, quality control and experience from more than 200 routine productions. EJNMMI radiopharm. chem. 6, 4 (2021).

Lindner, S., Wängler, C., Bailey, J.J. et al. Radiosynthesis of [18F]SiFAlin-TATE for clinical neuroendocrine tumor positron emission tomography. Nat Protoc 15, 3827–3843 (2020).

Simon Lindner, Marcel Simmet, Franz Josef Gildehaus, Klaus Jurkschat, Carmen Wängler, Björn Wängler, Peter Bartenstein, Ralf Schirrmacher, Harun Ilhan. Automated production of [18F]SiTATE on a Scintomics GRP™ platform for PET/CT imaging of neuroendocrine tumors. Nuclear Medicine and Biology. (88-89)86-95.

Ilhan, H., Lindner, S., Todica, A. et al. Biodistribution and first clinical results of 18F-SiFAlin-TATE PET: a novel 18F-labeled somatostatin analog for imaging of neuroendocrine tumors. Eur J Nucl Med Mol Imaging 47, 870–880 (2020).

Connolly, D., Bailey, J. J., Ilhan, H., Bartenstein, P., Wängler, C., Wängler, B., Wuest, M., Wuest, F., Schirrmacher, R. 18F-Labeling of Radiotracers Functionalized with a Silicon Fluoride Acceptor (SiFA) for Positron Emission Tomography. J. Vis. Exp. (155), e60623, doi:10.3791/60623 (2020).

Ilhan, H., Todica, A., Lindner, S. et al. First-in-human 18F-SiFAlin-TATE PET/CT for NET imaging and theranostics. Eur J Nucl Med Mol Imaging 46, 2400–2401 (2019).

Ralf Schirrmacher, Vadim Bernard-Gauthier, Esther Schirrmacher, Justin J. Bailey, Klaus Jurkschat, Carmen Wängler, Björn Wängler. (2019) Silicon-based 18F-radiopharmaceuticals: from basic SiFA chemistry toward its clinical application. Progress in Fluorine Science. 551-574

Bernard-Gauthier, V.*; Lepage, M.; Waengler, B., Bailey, J. J.*; Liang, S. H.; Perrin, D.; Vasdev, N.; Schirrmacher, R. (2018). Recent advances in fluorine-18 radiochemistry: Focus on B-18F, Si-18F, Al-18F and C-18F radiofluorination via spirocyclic iodonium ylides. J Nucl Med. 59(4): 568-572.

Berke S*, Kampmann AL*, Wuest M, Bailey JJ*, Glowacki B, Wuest F, Jurkschat K, Weberskirch R, Schirrmacher R. (2017). 18F Radiolabeling and in vivo analysis of SiFA-derivatized polymeric core-shell nanoparticles. Bioconjugate Chemistry. 29(1): 1-11.

Bernard-Gauthier, V.*, Bailey, J.J.*, Liu, Z., Wängler, B., Wängler, C., Jurkschat, K., Perrin, D.M., Schirrmacher, R. (2016). From Unorthodox to Established: The Current Status of 18F-Trifluoroborate- and 18F-SiFA-Based Radiopharmaceuticals in PET Nuclear Imaging. Bioconjugate Chem. 27(2): 267-279.

Zhu, J.*, Li, S., Wängler, C., Wängler, B., Lennox, R.B., Schirrmacher, R. (2015). Synthesis of 3-chloro-6- ((4-(di-tert-butyl[18F]fluorosilyl)-benzyl)oxy)-1,2,4,5-tetrazine ([18F]SiFA-OTz) for Rapid Tetrazine-Based 18F-Radiolabeling. Chem. Comm.51: 12415-12418.

Niedermoser, S., Chin, J.*, Waengler, C., Kostikov, A., Bernard-Gauthier, V.*, Vogler, N., Soucy, J.P., McEwan, A.J., Schirrmacher, R., Waengler, B. (Schirrmacher and Waengler contributed equally and share last authorship). (2015). In vivo evaluation of 18F-SiFAlin modified TATE: A potential challenge for 68Ga-DOTATATE, the clinical gold standard for somatostatin receptor imaging with positron emission tomography (PET). Journal Nuclear Medicine. 56(7): 1100-5.

Litau, S., Niedermoser, S., Vogler, N., Roscher, M., Schirrmacher, R., Fricker, G., Wängler, B., Wängler, C. (2015). Next generation of SiFAlin-based TATE derivatives for PET imaging of SSTR-positive tumors: Influence of molecular design on in vitro SSTR binding and in vivo pharmacokinetics.. Bioconjugate Chem.26(12): 2350-9.

Bernard-Gauthier, V.*, Waengler, C., Schirrmacher, E., Kostikov, A., Jurkschat, K., Waengler, B., Schirrmacher, R. (2014). 18F-Labeled silicon-based fluoride acceptors-potential opportunities for novel positron emitting radiopharmaceuticals. Journal BioMed Research International http:// dx.doi.org/10.1155/2014/454503. 2014

Zhu, J.*, Chin, J.*, Wängler, C.*, Waengler, B., Lennox, R.B., Schirrmacher, R. (2014). Rapid 18F-labeling and loading of PEGylated gold nanoparticles for in vivo applications. Bioconjugate Chem.25(6): 1142-1150.

Koudih, R.*, Kostikov, A., Kovacevic, M., Jolly, D., Bernard-Gauthier, V.*, Chin, J.*, Jurkschat, K., Wängler, C, Wängler, B., Schirrmacher, R. (2014). Automated radiosynthesis of N-succinimidyl 3-(di-tertbutyl[(18)F]fluorosilyl)benzoate ([(18)F]SiFB) for peptides and proteins radiolabeling for positron emission tomography. Int. J. Appl. Radiat Isot.89: 146-150.

Zhu, J.*, Hiltz, J., Mezour, M.A., Bernard-Gauthier, V.*, Lennox, R.B., Schirrmacher, R. (2014). Facile covalent modification of a highly ordered pyrolytic graphite (HOPG) surface via inverse electron demand Diels-Alder Reaction. Chem. Mater.26(17): 5058-5062.

Lindner, S., Michler, C., Leidner, S., Rensch, C., Wängler, C., Schirrmacher, R., Bartenstein, P., Wängler, B. (2014). Synthesis and in Vitro and in Vivo Evaluation of SiFA-Tagged Bombesin and RGD Peptides as Tumor Imaging Probes for Positron Emission Tomography. Bioconjugate Chem.16(4): 738-749.

Zhu, J.*, Hiltz, J., Lennox, R.B., Schirrmacher, R. (2013). Chemical modification of single walled carbon nanotubes with tetrazine-tethered gold nanoparticles via a Diels-Alder reaction. Chem. Comm.49(87): 10275-10277.

Kostikov, A.P.*, Chin, J.*, Orchowski, K.*, Schirrmacher, E., Niedermoser, S., Jurkschat, K., Iovkova- Berends, L., Wängler, C., Wängler, B., Schirrmacher, R. (2012). Synthesis of [(18)F]SiFB: a prosthetic group for direct protein radiolabeling for application in positron emission tomography. Nat. Protoc.7(11): 1956-1963.

Kostikov, A.P.*, Chin, J.*, Orchowski, K.*, Niedermoser, S., Kovacevic, M.M., Aliaga, A., Jurkschat, K., Wängler, B., Wängler, C.*, Wester, H.J., Schirrmacher, R. (2012). Oxalic acid supported Si-18Fradiofluorination: one-step radiosynthesis of N-succinimidyl 3-(di-tert-butyl[18F]fluorosilyl)benzoate ([18F]SiFB) for protein labeling. Bioconjugate Chem.23(1): 106-114.

Wängler, B., Kostikov, A.P.*, Niedermoser, S., Chin, J.*, Orchowski, K.*, Schirrmacher, E., Iovkova- Berends, L., Jurkschat, K., Wängler, C.*, Schirrmacher, R. (2012). Protein labeling with the labeling precursor [(18)F]SiFA-SH for positron emission tomography. Nat. Protoc.7(11): 1964-1969.

Wängler, C.*, Niedermoser, S., Chin, J.*, Orchowski, K.*, Schirrmacher, E.*, Jurkschat, K., Iovkova- Berends, L., Kostikov, A.P.*, Schirrmacher, R., Wängler, B. (2012). One-step (18)F labeling of peptides for positron emission tomography imaging using the SiFA methodology. Nat. Protoc.7(11): 1946-1955.

Kostikov, A.*, Iovkova, L., Chin, J.*, Schirrmacher, E., Waengler, B., Waengler, C.*, Jurkschat, K., Cosa,, Schirrmacher, R. (2011). N-(4-(di-tert-butyl[18F]fluorosilyl)benzyl)-2-hydroxy-N,N-dimethylethylammonium bromide: A novel lead compound for the development of hydrophilic SiFA-based prosthetic groups for 18Flabeling. J Fluorine Chem.132(1): 27-34.

Iovkova-Berends, L., Wängler, C.*, Zöller, T., Höfner, G., Wanner, K.T., Rensch, C., Bartenstein, P., Kostikov, A.*, Schirrmacher, R., Jurkschat, K., Wängler, B. (2011). t-Bu2SiF-derivatized D2-receptor ligands: the first SiFA-containing small molecule radiotracers for target-specific PET-imaging. Molecules.16(9): 7458-7479.

Wängler, C.*, Waser, B., Alke, A., Iovkova, L., Buchholz, H.G., Niedermoser, S., Jurkschat, K., Fottner, C., Bartenstein, P., Schirrmacher, R., Reubi, J.C., Wester, H.J., Wängler, B. (2010). One-step ¹⁸F-labeling of carbohydrate-conjugated octreotate-derivatives containing a silicon-fluoride-acceptor (SiFA): in vitro and in vivo evaluation as tumor imaging agents for positron emission tomography (PET). Bioconjugate Chem.21(12): 2289-2296.

Wängler B , Quandt G , Iovkova L , Schirrmacher E , Wängler C , Boening G , Hacker M , Schmoeckel M ,Jurkschat K , Bartenstein P , Schirrmacher R. (2009). Kit-like 18F-labeling of proteins: synthesis of 4-(ditert-butyl[18F]fluorosilyl)benzenethiol (Si[18F]FA-SH) labeled rat serum albumin for blood pool imaging with PET. Bioconjugate chemistry. 20(2)

Iovkova L , Wängler B , Schirrmacher E , Schirrmacher R , Quandt G , Boening G , Schürmann M ,Jurkschat K. (2009). para-Functionalized aryl-di-tert-butylfluorosilanes as potential labeling synthons for (18)F radiopharmaceuticals. Chemistry (Weinheim an der Bergstrasse, Germany). 15(9)

Schirrmacher E , Wängler B , Cypryk M , Bradtmöller G , Schäfer M , Eisenhut M , Jurkschat K ,

Schirrmacher R. (2007). Synthesis of p-(di-tert-butyl[(18)F]fluorosilyl)benzaldehyde ([(18)F]SiFA-A) with high specific activity by isotopic exchange: a convenient labeling synthon for the (18)F-labeling of N-aminooxy derivatized peptides. Bioconjugate chemistry. 18(6).

Schirrmacher R , Bradtmöller G , Schirrmacher E , Thews O , Tillmanns J , Siessmeier T , Buchholz HG , Bartenstein P , Wängler B , Niemeyer CM , Jurkschat K. (2006). 18F-labeling of peptides by means of an organosilicon-based fluoride acceptor. Angewandte Chemie (International ed. in English). 45(36).